TW516965B - A cosmetic light-screening composition for protecting human skin or human hair against ultraviolet radiation and novel sunscreening agents - Google Patents
A cosmetic light-screening composition for protecting human skin or human hair against ultraviolet radiation and novel sunscreening agents Download PDFInfo
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- TW516965B TW516965B TW087116339A TW87116339A TW516965B TW 516965 B TW516965 B TW 516965B TW 087116339 A TW087116339 A TW 087116339A TW 87116339 A TW87116339 A TW 87116339A TW 516965 B TW516965 B TW 516965B
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- cosmetic composition
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 35
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000000516 sunscreening agent Substances 0.000 title claims description 28
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- 238000012216 screening Methods 0.000 title abstract 2
- 150000001875 compounds Chemical group 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
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- 230000000475 sunscreen effect Effects 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 17
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- 238000010521 absorption reaction Methods 0.000 claims description 10
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- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 1
- DDDXLGRFOJHKMT-UHFFFAOYSA-N benzene;2-butylphenol Chemical compound C1=CC=CC=C1.CCCCC1=CC=CC=C1O DDDXLGRFOJHKMT-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940049657 cyclomethicone 5 Drugs 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 150000001954 decanoic acid esters Chemical class 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940074050 glyceryl myristate Drugs 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- LGCUKQRMISIOOC-UHFFFAOYSA-N octadecanoic acid propanedioic acid Chemical compound OC(=O)CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O LGCUKQRMISIOOC-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940116987 ppg-3 myristyl ether Drugs 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Abstract
Description
516965516965
五、發明說明(1) 本發明係關於一種防曬化链 合物用以保護人類皮膚和人類 28 0和40 0毫微米的紫外光傷害 合物及這些化合物作為UV濾劑 已經知道日光加速皮膚老化 不欲的效果係由UV射線引發。 品組合物,此防曬化粧品組 頭髮使其免受波長介於約 之用途’組合物中含有的化 方面的用途。 ,甚至引發皮膚癌,這些所 現在發現式I化合物V. Description of the invention (1) The present invention relates to a sun-protecting chain used to protect human skin and human ultraviolet light damage compounds of 280 and 400 nm, and these compounds have been known as UV filters to accelerate skin aging. The unwanted effect is caused by UV rays. This sunscreen cosmetic composition protects the hair from the use of chemical substances contained in the composition. , And even cause skin cancer, these are now found compounds of formula I
I 其中, R:代,Ci-8直鏈或帶有支鏈的烷基鏈,而 R2和R3分別代表(^_8直鏈或帶有支鏈的烷基鏈,是極佳的 UV濾劑,其具有皮膚配伍性和安定性(光、熱、濕氣);它 們使得皮膚有強烈的UV保護性並因此能夠延緩皮膚老化= 特別地,這些UV濾劑也具有箸g越的光穩定性。 。 雖然式I化合物的最大吸收不在此範圍,而是在約3 2 〇至 34 0毫微米,即,介於UVA和ϋνβ射線最大吸收之間,作 疋,已經知道式I化合物有最大吸收出現於— Α波長者 (如:4-第三丁基-4,-曱氧基二琴醯基曱烷)和出現於” 波長且特別並另人訝異地提高UV-B光保護效果者(即, 要吸收製造紅斑之約2 9 0至約3 2 0毫微米的Uv — B射線者,)主 亦能夠吸收這些範圍之可用於化粧品應用 川上的唯一類型I Among them, R: Generation, Ci-8 straight or branched alkyl chain, and R2 and R3 respectively represent (^ _8 straight or branched alkyl chain, which is an excellent UV filter , They have skin compatibility and stability (light, heat, moisture); they make the skin have strong UV protection and therefore can delay skin aging = In particular, these UV filters also have a light stability of 箸 g Although the maximum absorption of the compound of formula I is not in this range, but is about 32 to 300 nanometers, that is, between the maximum absorption of UVA and βνβ rays, it is known that the compound of formula I has the maximum absorption. Appear at — wavelengths of A (such as: 4-tert-butyl-4, -fluorenyldimethylenoxane) and those who appear at “wavelengths” that specifically and surprisingly increase UV-B photoprotective effects (Ie, those who want to absorb about 290 to about 320 nanometers of Uv-B rays that make erythema,) the owner can also absorb these ranges of the only type that can be used in cosmetic applications
C:\DATA\DATA29\54057.ptdC: \ DATA \ DATA29 \ 54057.ptd
516965 五、發明說明(2) 是二苯曱綱和鄰-胺基苯曱酸旨。許多調配物不被採用 的原因如··萃出量比式I化合物少得多。 式I的烧氧基苯胺基伸曱基丙二酸酯可由⑽^^^^· 3,0 7 9,3 6 6 和 W.O.Kermack,N.E.St〇rey,】·⑶亂 Soc· 607 (1950) ;Τ· Takahashi, S· Senda, j· pharm. s〇c· Jpn·, 71, 1 1 1 2 ( 1 952 )得知。被特別提到的有甲氧基_、 乙^基-和丁氧基—苯胺基—伸曱基丙二酸乙酯。但未曾提 及这些化合物於化粧品應用上之使用,特別是未曾提及這 些化合物於皮膚保養或人類頭髮保養方面之使用。 曲UV濾劑在化粧品溶劑中的溶解度應夠大,以調配成合理 ’辰度。例如,在水含量70% ' uv_之濾劑含量6%之典型的油 於水中礼劑中,於油相中之溶解度必須高至20%。令人訝 異地,已經發現到式1化合物在許多化粧品溶劑(如:辛酸 癸,1油三酸酯、丙二醇二辛酸酯二癸酸酯、Cl^5烷基笨 曱I S曰、丙一酸一硬脂酸酯、二異丙酸己二酸酯之類)中 的溶解度高至20%。 +據此本發明之目的係關於新穎的式I化合物,包含至 H刚述式I化合物(以與至少_種叮β渡劑和至少一種 ^併用為佳)之用於化粧品用途的防曬製劑,及式I 化::為防曬劑(特別是於化粧品用途方面)之使用。 其免受紫外光傷種用以?護人類皮膚或人類頭髮使 ,α 的防曬化粧σσ組合物’其中含有處於化 说口口用途上可技成 」接又的载體中之至少一種式I化合物516965 V. Description of the invention (2) It is intended for diphenylhydrazones and o-aminobenzoic acid. Many formulations are not used for reasons such as: · The amount of extraction is much less than the compound of formula I. The oxyanilino arsenylmalonate of formula I can be obtained from ⑽ ^^^^ 3, 0 7 9, 3 6 6 and WOKermack, NEStOrey,] · CD Chao Soc · 607 (1950); T. Takahashi, S. Senda, j. Pharm. Soc. Jpn., 71, 1 1 1 2 (1952). Special mention is made of methoxy-, ethyl-, and butoxy-aniline-ethenyl malonate. However, the use of these compounds in cosmetic applications has not been mentioned, and in particular the use of these compounds in skin care or human hair care has not been mentioned. The solubility of curved UV filters in cosmetics solvents should be large enough to be formulated to a reasonable degree. For example, in a typical oil in water solution with a water content of 70% and a filter content of 6%, the solubility in the oil phase must be as high as 20%. Surprisingly, compounds of formula 1 have been found in many cosmetic solvents (such as: caprylic acid, oleyl trioleate, propylene glycol dicaprylate dicaprate, Cl ^ 5 alkylbenzene, IS Acid monostearate, diisopropyl adipate, etc.) solubility up to 20%. + Accordingly, the object of the present invention is a novel sunscreen preparation for cosmetic use, which comprises a novel compound of formula I, including the compound of formula I described above (preferably in combination with at least one kind of β-dose beta agent and at least one type), Formula I: It is the use of sunscreen (especially for cosmetics). Is it protected from UV light? Protecting human skin or human hair, the α sunscreen makeup σσ composition ’contains at least one compound of the formula I in a mouth-to-mouth application that can be used for oral applications.
C:\DATA\DATA29\54057.ptd 〜C: \ DATA \ DATA29 \ 54057.ptd ~
516965 五、發明說明(3) ρ】516965 V. Description of the invention (3) ρ]
Η Ν, CO.R2 CO,R3 其中, R1代表Cps直鏈或帶有支鏈的烷基鏈,而 R2和R3分別代表Cil直鏈或帶有支鏈的烷基鏈。 所謂n CV8直鏈或帶有支鏈的烷基鏈”是指如甲基、乙 基、正丙基、異丙基、正丁基、第三丁基、戊基、己基、 2 -乙基己基之類。 較佳的化合物是其R2和R3分別代表曱基、乙基、戊基或 2-乙基己基者。 R1基較佳為甲基、乙基或正丁基。 因此,以下列化合物為佳·· 其R1、R2和R3是曱基(實例1 )或乙基(實例4)的化合物;或 其R1是乙基而R2和R3是曱基(實例2)或2-乙基己基(實例6) 的化合物;或 其R1是正丁基而R2和R3是曱基(實例3 )或乙基(實例5 )的化 合物。 最佳者是根據實例4的化合物,其中,R1、R2和R3是乙 基。 此防曬化粧品組合物包含0 . 1至1 0重量% (以0 . 5至5重量 %為佳)的式I化合物,特別是包含1至3重量%式1化合物。 此防曬化粧品組合物可以另包含至少一種最大吸收位於Η Ν, CO.R2 CO, R3 where R1 represents Cps straight or branched alkyl chain, and R2 and R3 represent Cil straight or branched alkyl chain, respectively. The so-called n CV8 straight or branched alkyl chain "means, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, third butyl, pentyl, hexyl, 2-ethyl Hexyl and the like. Preferred compounds are those in which R2 and R3 represent fluorenyl, ethyl, pentyl, or 2-ethylhexyl, respectively. R1 is preferably methyl, ethyl, or n-butyl. Therefore, the following Compounds are preferred ... Compounds in which R1, R2 and R3 are fluorenyl (Example 1) or ethyl (Example 4); or R1 is ethyl and R2 and R3 are fluorenyl (Example 2) or 2-ethyl A compound of hexyl (Example 6); or a compound of which R1 is n-butyl and R2 and R3 are fluorenyl (Example 3) or ethyl (Example 5). The best is the compound according to Example 4, wherein R1, R2 And R3 are ethyl. This sunscreen cosmetic composition contains 0.1 to 10% by weight (preferably 0.5 to 5% by weight) of a compound of formula I, especially 1 to 3% by weight of a compound of formula 1. This The sunscreen cosmetic composition may additionally contain at least one maximum absorption
C:\DATA\DATA29\54057.ptd 第7頁 516965 五、發明說明(4) 約3 0 0至320毫微米的UV-B濾劑及至少一種最大吸收^340 毫微米(特定言之,介於340和360毫微米之間,更特別是 位於3 5 6毫微米)的U V - A濾劑。特定言之,此u V - A -濾劑是 4-第三丁基-4’ -甲氧基二车醯曱烷。通常,此UV-Α劑可以 選自2-曱基二亨醯基曱烷、4-曱基二罕醯基甲烷、4-第三 丁基一卞醯基曱烧、2,4-一曱基二丰醯基甲烧'2,5 -二甲 基二$酿基曱烷'4, 4’-二異丙基二窄醯基曱烷、4-第三 丁基-4’:曱氧基二琴醯基曱烷、2-曱基_5 -異丙基-4,-曱 氧基一卞醯基曱烧、2_曱基-5-第三丁基_4’_曱基二亨醯 基曱烷、2, 4 -二曱基-4’-曱氧基二窄醯基曱烷和2,6一二曱 基-4-第二丁基-4 -曱氧基二卞^基〜曱烷及對笨亞二曱基 二樟腦續酸。 此UV-B濾劑是選自下列之至少—者:肉桂酸醋、二笨曱 銅、二笨基丙烯酸三嗪、樟腦衍生物、聚合型訂吸收劑 „述appllcation us 5 4〇3 9“中者) 少一者·钿、错 ^ 处斗 此1^ —B濾劑是自下列之至 J 有·錦 鐵、欽、鋅或4 士 物顏料及具烴結構或帶有至小一、別是鈦或鋅)的金屬氧化 烷結構的聚合物。 個紫外光吸收基團之矽氧 防曬化粧品組合物或式I化八私 人類頭髮使其免受紫外光傷害"。句可用以保護人類皮膚或 下列式I化合物是新穎的化合物· 2 -(4-庚氧基-笨胺基伸甲基)丙二 2 -(4-曱氧基-笨胺基伸甲 - 曰 丞)丙二酸二曱酯,C: \ DATA \ DATA29 \ 54057.ptd Page 7 516965 V. Description of the invention (4) UV-B filter of about 300 to 320 nanometers and at least one maximum absorption ^ 340 nanometers (specifically, the medium UV-A filters between 340 and 360 nm, and more particularly at 3 5 6 nm). In particular, this uV-A-filter is 4-tert-butyl-4'-methoxydicarboxane. Generally, this UV-A agent can be selected from 2-fluorenyldihexylfluorenylmethane, 4-fluorenyldihenylmethane, 4-tert-butylmonofluorenylmethane, 2,4-monofluorenyldiamine Phenylmethanine '2,5-Dimethylbis-methylpyrrolidine'4, 4'-diisopropyldi-n-pyridylpyrene, 4-tert-butyl-4': fluorenyldioxane Sulfenylhaloxane, 2-fluorenyl-5 -isopropyl-4, -fluorenyl-monomethylfluorenyl, 2-fluorenyl-5-tert-butyl-4'_fluorenyldihenylfluorenyl Alkane, 2, 4-difluorenyl-4'-fluorenyldi-n-fluorenylfluorene, and 2,6-difluorenyl-4-second-butyl-4-fluorenyldifluorenyl ~ fluorane And stearic acid. This UV-B filter is at least one selected from the group consisting of cinnamate, dibenzyl copper, dibenzyl acrylate triazine, camphor derivatives, polymer-type absorbers, and the above-mentioned appllcation us 5 4〇3 9 " The one) less one, 钿, wrong ^ doudou this 1 ^ —B filter is from the following to J Yes · Jintie, Chin, Zinc, or 4 pigments with hydrocarbon structure or with a small one, Other than titanium or zinc) metal alkylene oxide polymer. Silicone sunscreen cosmetic composition with a UV absorbing group or human hair protected from UV light ". Sentences can be used to protect human skin or the following compounds of formula I are novel compounds: 2- (4-heptyloxy-benzylaminomethyl) propanedi-2- (4-methyloxy-benzylaminomethyl)- Dimethyl malonate,
$ 8頁 C:\DATA\DATA29\54057.ptd 516965 五、發明說明(5) 2-(4 -乙氧基-笨胺基伸甲基)丙二酸二甲酯, 2 -(4_丙氧基-苯胺基伸曱基)丙二酸二曱酯’ 2-(4- 丁氧基-苯胺基伸曱基)丙二酸二曱酯, 2-(4 -戊氧基-苯胺基伸曱基)丙二酸二曱酯, 2-(4-己氧基-苯胺基伸曱基)丙二酸二曱酯, 2-(4-乙氧基-苯胺基伸甲基)丙二酸二戊酯, 2-(4-乙氧基-笨胺基伸曱基)丙二酸乙酯戊酯, 2 -(4_乙氧基-苯胺基伸曱基)丙二酸二_2-乙基己醋及 2-(4_乙氧基_苯胺基伸曱基)丙二酸乙醋2_乙基己醋。 這些中的每一者可作為UV濾、劑,特定言之,可用於前述 的化粧品用途上。此處,對下列者特別感興趣: 2-(4-乙氧基-苯胺基伸曱基)丙二酸二戊酷, 2-(4-乙氧基-笨胺基伸曱基)丙二酸乙酯戊酯, 2-(4-乙氧基-苯胺基伸曱基)丙二酸二-2-乙基己酯,和 2-(4-乙氧基-苯胺基伸甲基)丙二酸乙酯2-乙基己酯。 以式I表示的化合物(已知及新化合物)可藉由 US 3,0 7 9,3 6 6中所述的傳統方法簡便製得,其製法如下: 苯胺衍生物(Ci-q烷氧基笨胺)與經適當取代的烷氧基伸 烧基丙二酸衍生物在有或無溶劑的情況下反應。 至於可用於本發明之防曬劑之化粧品用途上可接受的載 體,可以是符合化粧品要求之任何慣用的製劑,如:乳 霜、化粧水、乳劑、膏藥、膠、溶液、喷霧、膏狀物和乳 液;請參考,如:Kosmetik,Entwi cklung, Herstellung and Anwendung Kosmetischer Mittel 編輯,Wilfried$ 8 pages C: \ DATA \ DATA29 \ 54057.ptd 516965 V. Description of the invention (5) Dimethyl 2- (4-ethoxy-benzylamino) malonate, 2- (4-propoxyl) -Anilinophenylenediyl) malonyl malonate '2- (4-butoxy-anilinolidenyl) malonate, 2- (4-pentyloxy-anilinolidene) propyl Diacid diacid, 2- (4-hexyloxy-anilidene) dimalonate, 2- (4-ethoxy-anilinomethyl) malonate, 2- (4-ethoxy-benzylaminophenyl) ethyl malonate pentyl, 2- (4-ethoxy-anilinylphenyl) malonate di_2-ethylhexanoate and 2- ( 4_ethoxy_anilinophenyl) ethyl malonate 2-ethylhexyl acetate. Each of these can be used as a UV filter, agent, and in particular, can be used for the aforementioned cosmetic applications. Here, the following are of particular interest: 2- (4-ethoxy-anilinolidene) dimalonyl malonate, 2- (4-ethoxy-benzylidenephenylarylene) malonate Ester Amyl Ester, 2- (4-Ethoxy-anilidene) di-2-ethylhexyl malonate, and 2- (4-ethoxy-anilinomethyl) malonate 2-ethylhexyl ester. Compounds (known and new compounds) represented by Formula I can be easily prepared by the conventional method described in US 3,0 7,9,3 6 6 as follows: Aniline derivative (Ci-q alkoxy Benzylamine) reacts with a suitably substituted alkoxydialylmalonic acid derivative with or without a solvent. As for the cosmetically acceptable carrier that can be used for the sunscreen agent of the present invention, it can be any conventional preparation that meets the requirements of cosmetics, such as: cream, lotion, emulsion, plaster, gum, solution, spray, paste And lotions; see, for example: Kosmetik, Entwicklung, Herstellung and Anwendung Kosmetischer Mittel, Wilfried
C:\DATA\DATA29\54057.ptd 第9頁 516965 丨五、發明說明(6)C: \ DATA \ DATA29 \ 54057.ptd Page 9 516965 丨 V. Description of Invention (6)
Umbach, Georg Thieme Vertrag Stuttgart - New York 1 9 8 8; Sunscreens , Development, Evu1 at i on and Regulatory Aspects, ed. N. Y. Lowe, N. A. Shaat, Marcel Decker, Inc· New York Basel, 1990 0 由於它們的親脂性,式I化合物在含油和含脂的化粧品 製劑中之摻合良好。 由於它們的親脂性,新穎的化合物符合此處所須的標 準,即,在化粧品溶劑(如:M i g 1 y ο 1 8 1 2 N (辛酸癸酸甘 油三酸酯)、Miglyol 840 (丙二醇二辛酸酯二癸酸酯)、 Finsolv TN (C12_15 烷基苯曱酸酯)、Prisorine 203 4 (丙 二酸一硬脂酸酯)或Crodamol Μ (二異丙酸己二酸酯)中 之溶解度。 | 就前述觀點,特別佳是實例4的化合物。 適當情況下,此防曬化粧品製劑可以是油、化粧水、 i 膠、固體膏和乳劑(如:乳霜、乳液或離子性或非離子性 | 親脂性脂質之有小氣泡的分散液)、氣溶膠、喷霧、泡 |沫、粉末、洗髮精、潤髮乳或漆或化粧品之類的形式。 I 用以保護人類頭髮的化粧品製劑製自至少一種式I化合 丨 |物時,此適當的製劑是洗髮精、潤髮乳、化被水膠、乳 ; 丨膠、分散k、染髮劑之類。所有這些調配物的製劑為嫻於 丨此技藝之人士所習知。 ! ; ί 嫻於此技藝之人士已經知道的溶劑可用以製備這些形 丨式,如:油、蠟、醇、多元醇。所用之較佳的物劑是脂肪丨 丨酸、酯、脂肪醇,但也可以是乙醇、異丙醇、丙二醇、甘;Umbach, Georg Thieme Vertrag Stuttgart-New York 1 9 8 8; Sunscreens, Development, Evu1 at i on and Regulatory Aspects, ed. NY Lowe, NA Shaat, Marcel Decker, Inc. New York Basel, 1990 0 because of their lipophilicity The compound of formula I is well blended in oily and faty cosmetic preparations. Because of their lipophilicity, novel compounds meet the criteria required here, namely, in cosmetic solvents (eg Mig 1 y ο 1 8 1 2 N (caprylic capric triglyceride), Miglyol 840 (propylene glycol dicaprylyl Soluble in didecanoate), Finsolv TN (C12_15 alkyl benzoate), Prisorine 203 4 (malonate monostearate) or Crodamol M (diisopropyl adipate). In view of the foregoing, particularly preferred is the compound of Example 4. Where appropriate, this sunscreen cosmetic preparation may be oil, lotion, gelatin, solid cream, and emulsion (eg, cream, lotion, or ionic or non-ionic | Dispersions of lipophilic lipids with small bubbles), aerosols, sprays, foams, powders, shampoos, shampoos or lacquers or cosmetics. I Cosmetic preparations for protecting human hair From at least one compound of formula I, this suitable formulation is shampoo, conditioner, hydrogel, milk; gel, dispersion, hair dye, etc. The formulations for all these formulations are Known by those in this skill.!; Ί Solvents already known to those skilled in the art can be used to prepare these forms, such as: oils, waxes, alcohols, polyols. The preferred agents are fatty acids, esters, fatty alcohols, but can also be Ethanol, isopropanol, propylene glycol, and glycerine;
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五、發明說明(7) ' ~〜___ —~- -— 油之類。 此化粧品調配物可以另含有輔 釋劑、軟化劑、保濕劑、表面&其他溶劑、稀 香料、油1、低碳多元醇和單劑、消泳劑、 著色劑和顏料之類。 工基知、推進劑、矽酮、 此新穎的防曬組合物或式;!化合物 此技藝之人士可以自由地由前述者n點基於嫻於 但uv-A濾劑中,最佳的訂 — A濾劑是4—特丁」υν一A,劑。 亨醯基甲烷,其特別用以與2-( 、 土—曱乳基二 二酸二乙醋併用。 乙乳基本胺基伸甲基)丙 由下列貫例揭示其他優點、特·•徵和細節。 實例1 2-(4-曱氧基—笨胺基伸曱基)丙二酸二曱西旨 於室溫攪拌的情況下,在丨2· 3克(〇·丨莫耳)對—曱氧笨胺 的50毫升乙醇溶液中,逐滴添加17· 4克(〇·丨莫耳)甲氧美 伸曱士基丙二酸二甲_的70毫升乙醇溶液。於此溫度再授^ 1小%之後,反應混合物以冰浴冷卻,自行結晶出產物。 藉過濾而分離此粗製的固體物質,以乙醇清洗,得到12 9 克標題產物,其為白色固體,熔點89-9KC · (E: 8 9 9 )。 宅来 實例2 2一(4~乙氧基-笨胺基伸曱基)丙二酸二曱醋 製程與實例1相同,但以一當量對—胺基笨乙_ 曱氧笨胺。得到1 9· 8克標題產物,其為白色固μ 1對一 巴U ,熔點是V. Description of the invention (7) '~~ ___ — ~--— Oil and the like. This cosmetic formulation may additionally contain auxiliary release agents, softeners, humectants, surface & other solvents, thinners, oils, low-carbon polyols and single agents, anti-swim agents, colorants, pigments and the like. GK, propellant, silicone, this novel sunscreen composition or formula; Compounds The person skilled in the art can freely use the above-mentioned n-points based on the best, but among the UV-A filters, the best order-A filter is 4-Tetin "νν-A, agent. Hexenyl methane, which is especially used in combination with 2- (, earth-lactamyl diacetic acid diethyl vinegar. Ethyl milk basic aminomethyl) propane, has the following advantages to reveal other advantages, characteristics and details . Example 1 2- (4-Methoxy-benzylaminobenzylidene) malonyl malonate is intended to be stirred at room temperature, and at 2 · 3g (〇 · 丨 mol) In a 50 ml ethanol solution of amine, 70 ml of a solution of 17.4 g (mole) of methomethoxyl malonate was added dropwise. After ^ 1% further at this temperature, the reaction mixture was cooled in an ice bath and the product crystallized out by itself. This crude solid material was separated by filtration and washed with ethanol to obtain 129 g of the title product as a white solid, melting point 89-9KC · (E: 8 9 9). Example 2 2 (4-ethoxy-benzylaminophenyl) malonate diacetate The process is the same as in Example 1, but with one equivalent of p-aminobenzyl-pyroxybenzamine. 19.8 g of the title product were obtained as a white solid μ 1 to 1 bar U with a melting point of
C:\DATA\DATA29\54057.ptci 第 11 頁 516965C: \ DATA \ DATA29 \ 54057.ptci Page 11 516965
五、發明說明(8) 6 6 - 6 7 °C ,UV 3 28 毫米(E = 8 7 9 ) 實例3 2-(4 - 丁氧基-苯胺基伸甲基)丙二酸二甲醋 a) 2-(4-羥基-苯胺基伸乙基)丙二酸二甲酯之製備 於室溫下,在16.4克(〇.15莫耳)4_胺基酚的1〇〇毫 醇溶液中逐滴添加26.1克(0.15莫耳)甲氧基伸甲基丙二 二甲酯的70毫升乙醇溶液。再於此溫度攪拌1〇分鐘之後, 過濾分離出粗製固體物質,以乙醇清洗,得到34. 3 固體’其未經純化便使用。 b) 溫中攪拌的情況下,在7克(28毫莫耳)的2— (4—羥 基-苯胺^基伸乙基)丙二酸二甲醑、3—· 9克(28毫莫耳)碳酸 部於50毫升一甲替曱醯胺中之说合物中,逐滴添加'3克 (2 8宅莫耳)丁基碘。此反應混合物於8 〇 t加熱2 4小時。之 後,反應混合物倒入5 〇毫升水中,以乙酸乙酯萃取三次。 有機層先後以氫氧化鈉溶液(15%)和水清洗,乾燥並蒸 發’得到4· 5克標題化合物,其為白色固體,熔點46-4? C ’UV 328 宅微米(e = 685)。 實例i 2 -(4-乙氧基-笨胺基伸曱基)丙二酸二乙酯 製程與實例1相同’但以一當量對-胺基笨乙醚代替對— 曱氧笨胺,並以一當量乙氧基伸甲基丙二酸二乙酯代替曱 氧基伸曱基丙二酸二曱酯。以己烷代替乙醇,得到2 克標 題產物’其為白色固體,熔點是55-56 °C ,UV 329毫米 (E二802)。V. Description of the invention (8) 6 6-6 7 ° C, UV 3 28 mm (E = 8 7 9) Preparation of dimethyl 2- (4-hydroxy-anilinoethyl) malonate at room temperature in a solution of 16.4 g (0.155 mol) of 4-aminophenol in 100 mmol A solution of 26.1 g (0.15 mol) of methoxymethylene dimethyl dimethyl ester in 70 ml of ethanol was added. After stirring at this temperature for 10 minutes, the crude solid material was separated by filtration and washed with ethanol to obtain 34.3 solid 'which was used without purification. b) In the case of warm stirring, at 7 grams (28 millimoles) of 2- (4-hydroxy-aniline ^ ylethenyl) malonyl malonate, 3 ·· 9 grams (28 millimoles) Carbonic acid was added to 50 ml of monomethylpyridamine, and 3 g (28 μmol) of butyl iodide was added dropwise. This reaction mixture was heated at 80 t for 24 hours. After that, the reaction mixture was poured into 50 ml of water and extracted three times with ethyl acetate. The organic layer was washed with sodium hydroxide solution (15%) and water, dried and evaporated to obtain 4.5 g of the title compound, which was a white solid with a melting point of 46-4? C 'UV 328 μm (e = 685). Example i 2-(4-ethoxy-benzylaminophenyl) malonyl diethyl malonate was prepared in the same manner as in Example 1 except that p-aminobenzyl ether was replaced with one equivalent of p-aminobenzyl ether, and An equivalent of diethyl ethoxymethylene malonate was used instead of dioxo dimethyl malonate. Replacing ethanol with hexane gave 2 g of the title product 'as a white solid with a melting point of 55-56 ° C and UV 329 mm (E = 802).
C:\DATA\DATA29\d4057.ptd 第 12 頁 516965 五、發明說明(9) 實例5 2 -(4- 丁氧基—笨胺基伸曱基)丙二酸二乙酯 製程與實例3相同,但以一當量乙氧基伸曱基丙二酸二 乙酯代替曱氧基伸曱基丙二酸二曱酯。得到3· 1克標題產 物’其為白色固體,熔點是54-55它,uv 3 2 9毫米 (E=714) 〇 ^ 實例6 2 -(4-乙氧基—笨胺基伸甲基)_丙二酸二__2—乙基己酯和 2-(4-乙氧基~笨胺基伸甲基)_丙二酸乙酯2_乙基己酯 18.4克(60毫莫耳)2 —(4-乙氧基-苯胺基伸甲基)_丙二 酸二乙醋、430毫克異丙氧化鈦<IV)於70毫升2-乙基一己 醇中之混^物於l5(rc攪拌4小時。此反應混合物於低壓 (8 0 C 6愛巴)’辰、%§以得到黃色油。此油溶解於1 〇 〇亳升乙 馱乙8曰和5耄升水中,攪拌1 〇分鐘,以無水硫酸鎂乾燥。 成片的懸浮液經過濾及於低壓濃縮,得到2 6 · 8克黃色油, 使用己烷··乙酸乙醋(10 : n作為沖提液,以加壓層析法 分離這兩種標題產物。 得到23. 6克的2-(4-乙氧基-笨胺基伸甲基)_丙二酸二 ―2:乙基己酯,其為黃色油,UV 3 2 9毫微米(Ε = 5 6 7 )。 得到1· 8克的2-(4-乙氧基—笨胺基伸曱基)—丙二酸乙酯 和2-乙基己酯,其為黃色油,ϋν 329毫微米(£二632)。C: \ DATA \ DATA29 \ d4057.ptd Page 12 516965 V. Description of the invention (9) Example 5 2-(4-butoxy-benzylaminophenyl) malonate diethyl ester The same process as in Example 3, However, one equivalent of diethyl ethoxylidenemalonate was used instead of diethyl alkoxylatemalonate. 3.1 g of the title product is obtained, which is a white solid with a melting point of 54-55, uv 3 2 9 mm (E = 714). Example 6 2-(4-ethoxy-benzylaminomethyl) _ Malonic acid di-2-ethylhexyl ester and 2- (4-ethoxy ~ benzylaminomethyl) _malonate ethyl 2-ethylhexyl ester 18.4 g (60 mmol) 2 — ( 4-Ethoxy-anilinomethyl) -diethyl malonate, 430 mg of titanium isopropoxide <IV) in 70 ml of 2-ethylmonohexanol was stirred at 15 (rc for 4 hours) The reaction mixture was obtained under low pressure (80 C 6 Aiba),% § to obtain a yellow oil. This oil was dissolved in 100 liters of ethyl acetate and 5 liters of water, and stirred for 10 minutes to Anhydrous magnesium sulfate was dried. The sliced suspension was filtered and concentrated under reduced pressure to obtain 26.8 g of a yellow oil, which was separated by pressure chromatography using hexane · ethyl acetate (10: n as the eluent). These two title products gave 23.6 g of 2- (4-ethoxy-benzylamino) -malonate di-2: ethylhexyl ester as a yellow oil, UV 3 2 9 mmol Micron (E = 5 6 7). 1.8 g of 2- (4-ethoxy-benzylaminophenylene) were obtained. - ethyl malonate and 2-ethylhexyl acrylate as a yellow oil, ϋν 329 nm (two £ 632).
實例J 2-U-乙氧基-笨胺基伸乙基)—丙二酸二戊酯和2_(4_乙氧 基-笨胺基伸乙基)-丙二酸乙酯戊酷Example J 2-U-ethoxy-benzylaminoethyl) -dipentyl malonate and 2- (4-ethoxy-benzylaminoethyl) -ethylmalonate
C:\DATA\DATA29\54057.ptd 第13頁 516965 五、發明說明(ίο) 其製程與實例6相同,但以正戊醇代替2-乙基-己醇。使 用己烷:乙酸乙酯(8 ·· 1)作為沖提液,以加壓層析法分離 兩種標題產物。 得到16. 6克的2-(4-乙氧基-苯胺基伸甲基)-丙二酸二戊 酯,其為黃色油,UV 329毫微米(E = 651)。 得到2. 5克的2-(4-乙氧基-苯胺基伸甲基)-丙二酸乙酯 戊酯,其為黃色油,UV 3 2 9毫微米(E = 725 )。C: \ DATA \ DATA29 \ 54057.ptd Page 13 516965 V. Description of the Invention (ίο) The process is the same as in Example 6, but n-pentanol is used instead of 2-ethyl-hexanol. Using hexane: ethyl acetate (8 ·· 1) as the eluent, the two title products were separated by pressure chromatography. 16.6 g of 2- (4-ethoxy-anilinomethyl) -malonate were obtained as a yellow oil, UV 329 nm (E = 651). 2.5 g of 2- (4-ethoxy-anilinomethyl) -ethyl malonate were obtained as a yellow oil, UV 3 2 9 nm (E = 725).
II C:\DATA\DATA29\540D7.ptd 第14頁 516965 五、發明說明(11) 實例8 製備製劑類型:水於油中之乳劑 成份 重量% A) 得自實例6的產物(二-2-乙基己酯) 6 丁基甲氧基二_醯基曱烷(Parsol 1789) 1.5 曱氧基丁二酸辛酯(Parsol MCX) 3 多甘油基-3-二異硬脂酸酯 5 油酸甘油酯 3 鯨蠟醇 2 礦油 10 椰子基辛酸/癸酸酯 10 經Dimethicone塗覆的二氧化鈦 2 辛基十二碳醇 2 丁基羥基曱苯 0.1 苯氧基乙醇、對-羥基苯酸曱酯、對-羥基苯酸乙酯和對羥基苯 0.6 酸丙酯及對-羥基苯酸丁酯 B) 甘油(86%) 5 苯基苯並咪唑磺酸(Parsol HS) 2 EDTA 二鈉 0.1 水 47.7 A部分和B部分分別於8 5 °C混合,之後在攪拌的情況下合 併。最後,必要時,以10%氫氧化鈉或1(3%檸檬酸將pH調整 至7。II C: \ DATA \ DATA29 \ 540D7.ptd Page 14 516965 V. Description of the invention (11) Example 8 Preparation of preparation type: Emulsion ingredient weight% in water in oil A) Product obtained from Example 6 (di-2- Ethylhexyl ester) 6 Butylmethoxydi-fluorenylmethane (Parsol 1789) 1.5 Octyl succinate (Parsol MCX) 3 Polyglyceryl-3-diisostearate 5 Glyceryl oleate 3 Cetyl Alcohol 2 Mineral Oil 10 Coco Caprylic Acid / Caprate 10 Dimethicone Coated Titanium Dioxide 2 Octyl Dodecyl Alcohol 2 Butyl Hydroxylbenzene 0.1 Phenoxyethanol, P-Hydroxybenzoate, P- Ethyl hydroxybenzoate and propyl p-hydroxybenzene 0.6 and butyl p-hydroxybenzoate B) Glycerin (86%) 5 Phenylbenzimidazole sulfonic acid (Parsol HS) 2 Disodium EDTA 0.1 Water 47.7 Part A and Part B was mixed separately at 85 ° C, and then combined with stirring. Finally, if necessary, adjust the pH to 7 with 10% sodium hydroxide or 1 (3% citric acid).
C:\DATA\DATA29\54057.ptd 第15頁 516965 五、發明說明(12) 實例9 製備製劑類型:水於油中之乳液(軟性乳霜) 成份 重量% A) 得自實例4的產物 5 POP-POE甘油山梨糖醇脂肪酸酯 5 伸庚基壬烧 5 石蠟 9 PPG-(15)-硬脂醇和 cyclomethicone 2 石夕石 0.4 丁基羥基甲苯 广 ^ 0.1 苯氧基乙醇、對-羥基苯曱酸曱酯、對-羥基苯曱酸乙酯和對-羥 0.6 基笨曱酸丙酯及對-羥基苯甲酸丁酯 B) 氯化鈉 0.5 POE-30山梨糖醇 1.5 甘油(8 6%) 2.5 EDTA 二鈉 0.1 水 68.3 A部分和B部分分別於85 °C混合,之後在攪拌的情況下合 併。最後,必要時,以10%氫氧化鈉或10%檸檬酸將pH調整 至7。C: \ DATA \ DATA29 \ 54057.ptd Page 15 516965 V. Description of the invention (12) Example 9 Preparation of preparation type: Water-in-oil emulsion (soft cream) Ingredient weight% A) Product from Example 4 5 POP-POE glycerol sorbitol fatty acid ester 5 heptyl nonane 5 paraffin wax 9 PPG- (15) -stearyl alcohol and cyclomethicone 2 stone evening stone 0.4 butylhydroxytoluene ^ 0.1 phenoxyethanol, p-hydroxybenzene Ethyl acetate, ethyl p-hydroxybenzoate and propyl p-hydroxybenzyl 0.6 and butyl p-hydroxybenzoate B) sodium chloride 0.5 POE-30 sorbitol 1.5 glycerol (8 6% ) 2.5 Disodium EDTA 0.1 Water 68.3 Part A and Part B were mixed at 85 ° C, and then combined with stirring. Finally, if necessary, adjust the pH to 7 with 10% sodium hydroxide or 10% citric acid.
C:\DATA\DATA29\54057.ptd 第16頁 516965 五、發明說明(13) 實例1 0 製劑類型:矽於水中之乳劑(乳液) 成份 重量% A) 得自實例5的產物 2 Cyclomethicone pentamere和經基硬脂酸#呂錤 9 Cyclomethicone 和 Dimethicone 共聚多元醇 10 Cyclomethicone 5 PPG-3肉豆蔻醚 2 經Dimethicone塗覆的二氧化鈦 2 C12-15烧基苯曱酸酯 10 丁基羥基曱苯 0.1 苯氧基乙醇、對-羥基苯甲酸曱酯、對-羥基苯甲酸乙酯和對-羥 0.6 基苯曱酸丙酯及對-羥基苯曱酸丁酯 B) 氯化鈉 0.5 醋酸生育酯 2 EDTA 二納 0.1 水 56.7 A部分和B部分分別於85°G混合,之後在攪拌的情況下合 | 併。最後,必要時,以1 0%氫氧化鈉或1 〇%擰檬酸將pH調整 至7。C: \ DATA \ DATA29 \ 54057.ptd Page 16 516965 V. Description of the invention (13) Example 1 0 Formulation type: Silicone in water emulsion (emulsion) Ingredient weight% A) Product obtained from Example 5 2 Cyclomethicone pentamere and Cyclomethicone # Lu 錤 9 Cyclomethicone and Dimethicone Copolyol 10 Cyclomethicone 5 PPG-3 Myristyl ether 2 Dimethicone-coated titanium dioxide 2 C12-15 alkylphenyl benzoate 10 Butyl hydroxybenzene benzene 0.1 phenoxy Ethyl alcohol, ethyl p-hydroxybenzoate, ethyl p-hydroxybenzoate and propyl p-hydroxybenzoate 0.6 and butyl p-hydroxybenzoate B) Sodium chloride 0.5 Tocopheryl acetate 2 EDTA II Sodium water 56.7 Part A and Part B were mixed at 85 ° G, and then combined with agitation. Finally, if necessary, adjust the pH to 7 with 10% sodium hydroxide or 10% citric acid.
第17頁 C:\DATA\DATA29\54057.ptd 516965 五、發明說明(14) 實例11 製劑類型:油於水中之乳劑 成份 重量% A) 得自實例4的產物 4 甲氧基肉桂酸辛酯(Parsol MCX) 3 丁基曱氧基二夸醯基曱烷(Parsol I789) 1.5 4-曱基笨亞甲基樟腦(Parsol 5000) 3 一肉豆蔻酸甘油酯 4 錄壤醇 一 一 1 椰子基辛酸/癸酸酯 15 肉豆蔻酸異丙酯 5 PVP-二十碳烯共聚物 2 丁基羥基曱苯 0.1 EDTA 二納 0.1 苯氧基乙醇、對-羥基苯甲酸甲酯、對-羥基苯曱酸乙酯和對-羥 0.6 基苯曱酸丙酯及對-羥基苯甲酸丁酯 B) POE-POP團聯共聚物 2 水 38.7 Carbomer 981 10 丙二醇 10 A部分和B部分分別於85 °C混合,之後在攪拌的情況下合 併。最後,必要時,以10%氫氧化鈉或10%檸檬酸將pH調整 至7。 -Page 17: C: \ DATA \ DATA29 \ 54057.ptd 516965 V. Description of the invention (14) Example 11 Formulation type: Emulsion content of oil in water by weight% A) Product obtained from Example 4 4 Octyl methoxycinnamate ( Parsol MCX) 3 butyl fluorenyl diquatyl fluorenoxane (Parsol I789) 1.5 4- fluorenylbenzylidene methylene camphor (Parsol 5000) 3 glyceryl myristate 4 Rhodonol -1 cocoyl caprylic acid / Decanoate 15 isopropyl myristate 5 PVP-eicosene copolymer 2 butylhydroxybenzoic acid 0.1 EDTA dinaphthalene 0.1 phenoxyethanol, methyl p-hydroxybenzoate, p-hydroxybenzoic acid Ethyl ester and propyl p-hydroxybenzoate and butyl p-hydroxybenzoate B) POE-POP block copolymer 2 Water 38.7 Carbomer 981 10 Propylene glycol 10 Parts A and B are mixed at 85 ° C, respectively. Combined with stirring afterwards. Finally, if necessary, adjust the pH to 7 with 10% sodium hydroxide or 10% citric acid. -
C:\DATA\DATA29\54057.ptd 第18頁 516965 五、發明說明(15) 實例1 2 製劑類型:油於水中之乳劑 成份 重量% A) 得自實例4的產物 3.5 甲氧基丁二酸辛酯(Parsol MCX) 3 丁基甲氧基二醯基甲烷(Parsol 1789) 1.5 4-曱基苯亞甲基樟腦(Parsol 5000) 3 一肉豆謹酸甘油醋 4 鯨蠟醇 1 椰子基辛酸/癸酸酯 ~ — 5 肉豆蔻酸異丙酯 5 PVP-二十碳烯共聚物 1 丁基羥基曱苯 0.1 EDTA 二鈉 0.1 苯氧基乙醇、對-羥基苯曱酸曱酯、對-羥基苯甲酸乙酯和對-羥 0.6 棊苯曱酸丙酯及對-羥基苯曱酸丁酯 B) 山梨糖醇酯和蔗糖酯 4 水 48.2 Carbomer 981 10 丙二醇 10 A部分和B部分分別於85 °C混合,之後在攪拌的情況下合 併。最後,必要時,以10%氫氧化鈉或10%擰檬酸將pH調整 至7。C: \ DATA \ DATA29 \ 54057.ptd Page 18 516965 V. Description of the invention (15) Example 1 2 Formulation type: oil-in-water emulsion ingredients% by weight A) Product obtained from Example 3.5 Caprylyl succinate Ester (Parsol MCX) 3 Butylmethoxydimethylmethane (Parsol 1789) 1.5 4-Methenylbenzylidene camphor (Parsol 5000) 3 Monomyristolic acid glycerol vinegar 4 Cetyl alcohol 1 Cocoyl caprylic acid / capric acid Esters ~ — 5 Isopropyl myristate 5 PVP-eicosene copolymer 1 Butyl hydroxybenzobenzene 0.1 EDTA disodium 0.1 phenoxyethanol, ethyl p-hydroxybenzoate, ethyl p-hydroxybenzoate Ester and 0.6-propyl p-hydroxybenzoate and butyl p-hydroxybenzoate B) Sorbitol and sucrose esters 4 Water 48.2 Carbomer 981 10 Propylene glycol 10 Parts A and B are mixed at 85 ° C, respectively. Combined with stirring afterwards. Finally, if necessary, adjust the pH to 7 with 10% sodium hydroxide or 10% citric acid.
C:\DATA\DATA29\54057.ptd 第19頁 516965 五、發明說明(16) 實例8、11和12的乳劑在約2 8 0至40 0毫微米的整個UV範 圍内顯現寬廣的濾光活性,最大吸收出現於約3 0 0至3 6 0毫 微米處。C: \ DATA \ DATA29 \ 54057.ptd Page 19 516965 V. Description of the invention (16) The emulsions of Examples 8, 11 and 12 exhibit broad filter activity over the entire UV range of about 280 to 400 nm The maximum absorption occurs at about 300 to 360 nm.
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DE19904329A1 (en) * | 1999-01-28 | 2000-08-03 | Cognis Deutschland Gmbh | Cosmetic and / or pharmaceutical preparations |
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EP1025836A1 (en) * | 1999-02-08 | 2000-08-09 | F. Hoffmann-La Roche Ag | Cosmetic light screening composition |
DE19937299A1 (en) * | 1999-08-06 | 2001-02-15 | Cognis Deutschland Gmbh | Sunscreen |
DE10063946A1 (en) | 2000-12-20 | 2002-07-04 | Basf Ag | Use of light stabilizer combinations which contain 2,2'-p-phenylene-bis (3,1-benzoxazin-4-one) as an essential constituent as a photostable UV filter in cosmetic and pharmaceutical preparations |
DE10063867A1 (en) * | 2000-12-21 | 2002-07-11 | Haarmann & Reimer Gmbh | Compositions for protecting human skin and hair against the damaging effects of ultraviolet radiation, comprise new or known N-substituted anilinomethylene malonic acid derivatives |
DE10113058A1 (en) | 2001-03-15 | 2002-09-19 | Basf Ag | Use of light stabilizer combinations which contain 2- (4-alkoxy-anilinomethylene) -malonic acid dialkyl esters as an essential constituent as photostable UV filters in cosmetic and pharmaceutical preparations |
DE10124332A1 (en) * | 2001-05-18 | 2002-11-21 | Basf Ag | Cosmetic or pharmaceutical preparations containing enaminotriazines as light stabilizers and new enaminotriazines |
DE10143964A1 (en) * | 2001-09-07 | 2003-03-27 | Basf Ag | Low-emulsifier or emulsifier-free systems of the oil-in-water type containing stabilizers and an amino-substituted hydroxybenzophenone |
DE10143960A1 (en) * | 2001-09-07 | 2003-03-27 | Basf Ag | Cosmetic and dermatological preparations in stick form, containing an amino-substituted hydroxybenzophenone |
DE10143963A1 (en) * | 2001-09-07 | 2003-03-27 | Basf Ag | Cosmetic and dermatological preparations in the form of W / O emulsions containing an amino-substituted hydroxybenzophenone |
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DE4122475A1 (en) * | 1991-07-06 | 1993-01-07 | Basf Ag | AMINOMETHYLENCYANESSIGESTER |
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US5639446A (en) * | 1996-09-20 | 1997-06-17 | 3V Inc. | Derivatives of benzoxazole useful as UV stabilizers |
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1998
- 1998-07-24 US US09/122,117 patent/US6069170A/en not_active Expired - Fee Related
- 1998-07-30 EP EP98114262A patent/EP0895776B1/en not_active Expired - Lifetime
- 1998-07-30 DK DK98114262T patent/DK0895776T3/en active
- 1998-07-30 CA CA002244556A patent/CA2244556A1/en not_active Abandoned
- 1998-07-30 DE DE69815449T patent/DE69815449T2/en not_active Expired - Fee Related
- 1998-07-30 ES ES98114262T patent/ES2198026T3/en not_active Expired - Lifetime
- 1998-08-03 CN CNB981167918A patent/CN1148165C/en not_active Expired - Fee Related
- 1998-08-04 JP JP10219930A patent/JPH11100318A/en active Pending
- 1998-08-04 ID IDP981090A patent/ID20678A/en unknown
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- 1998-08-04 BR BR9802837-5A patent/BR9802837A/en not_active Application Discontinuation
- 1998-08-04 AU AU78776/98A patent/AU739558B2/en not_active Ceased
- 1998-08-04 KR KR1019980031729A patent/KR100543269B1/en not_active IP Right Cessation
- 1998-10-01 TW TW087116339A patent/TW516965B/en not_active IP Right Cessation
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EP0895776A3 (en) | 1999-04-28 |
NO983581L (en) | 1999-02-08 |
CN1148165C (en) | 2004-05-05 |
NO983581D0 (en) | 1998-08-04 |
DE69815449D1 (en) | 2003-07-17 |
EP0895776B1 (en) | 2003-06-11 |
AU7877698A (en) | 1999-02-18 |
DK0895776T3 (en) | 2003-08-25 |
BR9802837A (en) | 2000-01-11 |
DE69815449T2 (en) | 2004-02-12 |
US6069170A (en) | 2000-05-30 |
NO312332B1 (en) | 2002-04-29 |
KR19990023356A (en) | 1999-03-25 |
CA2244556A1 (en) | 1999-02-05 |
CN1207290A (en) | 1999-02-10 |
EP0895776A2 (en) | 1999-02-10 |
ID20678A (en) | 1999-02-11 |
AU739558B2 (en) | 2001-10-18 |
JPH11100318A (en) | 1999-04-13 |
KR100543269B1 (en) | 2006-04-21 |
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